Citation: Li Jian, Hu Qi-Long, Chen Xue-Ping, Hou Ke-Qiang, Chan Albert S.C., Xiong Xiao-Feng. Asymmetric synthesis of tetrahydropyran[3, 2-c]quinolinones via an organocatalyzed formal[3 + 3] annulation of quinolinones and MBH 2-naphthoates of nitroolefin[J]. Chinese Chemical Letters, ;2020, 31(3): 697-700. doi: 10.1016/j.cclet.2019.08.040 shu

Asymmetric synthesis of tetrahydropyran[3, 2-c]quinolinones via an organocatalyzed formal[3 + 3] annulation of quinolinones and MBH 2-naphthoates of nitroolefin

Guangdong Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China

chenxz3@mail.sysu.edu.cn

xiongxf7@mail.sysu.edu.cn

Received Date: 5 July 2019
Revised Date: 8 August 2019
Accepted Date: 23 August 2019
Available Online: 23 August 2019

Figures(6)

An efficient asymmetric and enantio-swithchable organocatalytic[3 + 3] annulation reaction using MBH-2-naphthoates of nitroalkenes and 4-hydroxyquinolin-2(1H)-ones has been developed. Densely substituted tetrahydropyrano[3, 2-c]quinolinones scaffolds with two adjacent stereogenic centers are obtained with high yield (up to 95% yield) and good stereoselectivities (up to > 20:1 dr and 96% ee) in an enantio-switchable manner. Furthermore, gram scale synthesis was achieved and the nitro group could easily transform into an amino group without any appreciable loss in the diastereo-and enantioselectivity.
- Organocatalysis,
- Asymmetric synthesis,
- Enantioswitchable,
- Cinchona alkaloid,
- Tetrahydropyran[3, 2-c]quinolines
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